6307-67-1

Usage

Uses

Used in Pharmaceutical Industry:
2-chloro-N-(2-chloro-6-Methylphenyl)acetaMide is used as an intermediate in the synthesis of Butanilicaine Hydrochloride, a local anesthetic. It plays a vital role in the development of this anesthetic agent, which is used to numb specific areas of the body during medical procedures, providing pain relief and ensuring patient comfort.

InChI:InChI=1/C9H9Cl2NO/c1-6-3-2-4-7(11)9(6)12-8(13)5-10/h2-4H,5H2,1H3,(H,12,13)

Upstream product

• 79-04-9 chloroacetyl chloride 
• 87-63-8 2-chloro-6-methylaniline 
• 79-07-2 Chloroacetamide 

Downstream Products

• 108951-43-5 pyrrolidino-acetic acid-(2-chloro-6-methyl-anilide) 
• 110060-25-8 piperidino-acetic acid-(2-chloro-6-methyl-anilide) 
• 102169-22-2 N-benzyl-N-butyl-glycine-(2-chloro-6-methyl-anilide) 
• 50416-18-7 glycine-(2-chloro-6-methyl-anilide); hydrochloride 
• 70289-10-0 N,N-dimethyl-glycine-(2-chloro-6-methyl-anilide) 
• 3785-21-5 2-(butylamino)-N-(2-chloro-6-methylphenyl)acetamide 
• 107456-16-6 N-tert-butyl-glycine 2-chloro-6-methyl-anilide 
• 64893-09-0 (3-tert-butyl-2-oxo-2λ⁴-[1,2,3]oxathiazolidin-5-ylidene)-(2-chloro-6-methyl-phenyl)-amine 
• 101260-31-5 N-(diethylaminoethyl)-aminoacetic acid 2-chloro-6-methylanilide 
• 1186430-68-1 N-(2-chloro-6-methylphenyl)-2-[4-[3-(7,8-dimethoxy-1,3-dihydro-2H-3-benzazepin-2-on-3-yl)propyl]piperazinyl]acetamide 
• 1236306-22-1 N-(2-chloro-6-methylphenyl)-2-(4-(4-(pyridin-4-ylmethyl)phthalazin-1-yl)piperazin-1-yl)acetamide 
• 1236306-35-6 N-(2-chloro-6-methylphenyl)-2-(4-(4-benzylphthalazin-1-yl)piperazin-1-yl)acetamide 
• 302964-08-5 2-(6-chloro-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide 

Relevant academic research and scientific papers

Design and Synthesis of Novel Positive Allosteric Modulators of α7 Nicotinic Acetylcholine Receptors with the Ability to Rescue Auditory Gating Deficit in Mice

A series of novel thiazolo[4,5-d]pyrimidin-7(6H)-ones (3aa-3eq) were designed, synthesized, and evaluated as the type I positive allosteric modulators of human α7 nAChR expressed in Xenopus ooctyes by a two-electrode voltage clamp. The structure-activity relationship analysis identified the compound 3ea as a potent and efficacious PAM with the maximum activation effect of the α7 current of over 1633% in the presence of acetylcholine (100 μM) and an EC50 = 1.26 μM. It is highly specific to α7 nAChR over other subtypes of nAChR, 5-HT3A, NMDA, and GABAA receptors. Compound 3ea showed an elimination half-life of 10.8 ± 1.5 h for 3 mg/kg, i.v., and 7.4 ± 1.1 h for 60 mg/kg, i.g. in rat. It also exhibited sufficient blood-brain barrier penetration with no significant effect on hERG channel. Most importantly, compound 3ea dose-dependently (0.1-1 mg/kg, i.p.) reversed the prepulse inhibition deficit induced by MK-801 in the mouse schizophrenia model.

NOVEL KINASE INHIBITORS EXHIBITING ANTI-CANCER ACTIVITY AND THEIR METHOD OF USE

Pharmaceutical compositions of the invention comprise kinase inhibitors having a disease-modifying action in the treatment of diseases associated with BCR-ABL activity that include cancer, including chronic myeloid leukemia, acute lymphoblastic leukemia,

THIAZOLOPYRIMIDINONE COMPOUNDS AND PREPARATION METHODS AND USE THEREOF

The present invention provides structural details of a thiazolopyrimidinone compound, a preparation method thereof, and use thereof in the manufacture of a medicament for the treatment of central nervous system diseases.

Design and synthesis of novel 4'-demethyl-4-deoxypodophyllotoxin derivatives as potential anticancer agents

A group of podophyllotoxin (PPT) derivatives (7a-j) were synthesized by conjugating aryloxyacetanilide moieties to the 4'-hydroxyl of 4'-demethyl-4-deoxypodophyllotoxin (DDPT), and their anticancer activity was evaluated. It was found that the most potent compound 7d inhibited the proliferation of three cancer cell lines with sub to low micromolar IC50 values. Furthermore, it was demonstrated that 7d induced cell cycle arrest in G2/M phase in MGC-803 cells, and regulated the expression of cell cycle check point proteins, such as cyclin A, cyclin B, CDK1, cdc25c, and p21. Finally, 4 mg/kg of 7d reduced the weights and volumes of HepG2 xenografts in mice. Our findings suggest that 7d might be a potential anticancer agent.

Synthesis and biological activity of some 1,3-dihydro-2H-3-benzazepin-2- ones with a piperazine moiety as bradycardic agents

A series of 1,3-dihydro-2H-3-benzazepin-2-ones with a piperazine moiety were designed and synthesized by treating the common intermediate of 1,3-dihydro-7,8-dimethoxy-3-[3-(1-piperazinyl)-propyl]-2H-3-benzazepin-2-ones with a variety of N-aryl-2-chloroacetamides and acyl chlorides. Their structures have been characterized by 1H-NMR, MS, and elemental analysis. The title compounds were evaluated for their bradycardic activity in vitro. Most of the synthesized compounds exhibited some vasorelaxant activity and heart-rate-reducing activity with bradycardic potency.

Synthesis and antitumor activities of novel 1,4-disubstituted phthalazine derivatives

In an attempt to develop potent and selective antitumor agents,a series of novel 1,4-disubstituted phthalazine derivatives was designed and synthesized. All the prepared compounds were screened for their cytotoxic activities against A549,HT-29 and MDA-MB-231 cell lines in vitro. Among them,seven compounds (7a7e,7j and 7i) displayed excellent selectivity for MDA-MB-231 cells with IC50 values in the nM range,a desirable range for pharmacological testing. The most promising compound,7a (IC50 = 3.79 μ M,2.32 μ M,0.84 nM),was 5.6-,10.8-and 6.9 × 104-times more active than PTK-787 (IC50 = 21.16 μ M,22.11 μ M,57.72 μ M),respectively.

PROCESS FOR PREPARING N-(2-CHLORO-6-METHYLPHENYL)-2-[[6-[4-(2-HYDROXYETHYL)-1-PIPERAZINYL]-2-METHYL-4-PYRIMIDINYL]AMINO] -5-THIAZOLECARBOXAMIDE AND RELATED METABOLITES THEREOF

The present invention is directed to process for the preparation of metabolites as well as the parent compound of N-(2-chloro-6-methylphenyl)-2-[[6-[4-(2-hydroxyethyl)-1-piperazinyl]-2-methyl-4-pyrimidinyl] amino]-5-thiazolecarboxamide, the compound of formula (I).

THERAPEUTIC AGENT FOR URINARY INCONTINENCE

PROBLEM TO BE SOLVED: To provide a new higher safe compound having higher effectiveness against urinary incontinence with smaller adverse effects. SOLUTION: A prophylactic and/or therapeutic agent for the urinary incontinence comprises a compound represented by formula (I) {wherein, A is a single bond or methylene; E and G are each a lower straight-chain alkylene which may be substituted with a lower alkyl; m is 0-5; R1s are each a halogen, a CF3, an OCF3, a CN, an NO2, a carboxy, an OH, an SH, a lower alkoxycarbonyl, a (substituted) carbamoyl, a lower alkanoyloxy, a (substituted) sulfamoyl group or a lower alkyl group or the like which may be substituted with an ORa (wherein, Ra is an H or a lower alkyl), a COORa, an SRa or an N(Ra)2; R2, R3 and R4 are each an H or a lower alkyl; n is 0-5; R5s are each a CN, an NO2, a COOH, an SO3H, a lower alkoxycarbonyl, a lower alkanoyl or the like; R6 and R7 are each an H or a lower alkyl which may be substituted with an ORa or a COOH; or an NR6R7 is a 5- to a 6-membered saturated heterocyclic ring}, an optically active substance or a pharmacologically acceptable salt thereof as an active ingredient. The drug exhibits excellent effects on treatment and/or prophylaxis of the urinary incontinence without causing adverse effects on the cardiovacular system such as blood pressure elevation.

Synthesis and anticonvulsant activity of some ω-(1H-imidazol-1-yl)-N- phenylacetamide and propionamide derivatives

In this study, eight new ω-(1H-imidazol-1-yl)-N-phenylacetamide and propionamide derivatives having 2,6-dimethyl, 2,6-dichloro, 2-chloro-6-methyl and 2-isopropyl substitutions on N-phenyl ring were synthesized to evaluate anticonvulsant activity against maximal electroshock test. The most active compounds in the series were the derivatives bearing 2-isopropyl and 2,6-dimethyl substituents on N-phenyl ring.

The synthesis and anticonvulsant activity of some omega-phthalimido-N-phenylacetamide and propionamide derivatives.

In this study, by combining anilide and N', N'-phthaloylglycinamide pharmacophores which are known to produce potent anticonvulsant compounds, sixteen omega-phthalimido-N-phenylacetamide and propionamide derivatives bearing substituents at positions 2 or 2, 6 on N-phenyl ring have been synthesized. The structural confirmation of the title compounds was achieved by interpretation of spectral and analytical data. The anticonvulsant activity of the title compounds was determined against maximal electroshock seizure at 100 mg/kg dose level in mice. The preliminary screening results indicated that omega-phthalimido-N-phenylacetamide and propionamide nuclei have pronounced anticonvulsant activity against maximal electroshock seizure.